55096-86-1Relevant academic research and scientific papers
Reusable Co-nanoparticles for general and selectiveN-alkylation of amines and ammonia with alcohols
Beller, Matthias,Gawande, Manoj B.,Jagadeesh, Rajenahally V.,Kadam, Ravishankar G.,Li, Xinmin,Ma, Zhuang,Petr, Martin,Zbo?il, Radek,Zhou, Bei
, p. 111 - 117 (2022/01/06)
A general cobalt-catalyzedN-alkylation of amines with alcohols by borrowing hydrogen methodology to prepare different kinds of amines is reported. The optimal catalyst for this transformation is prepared by pyrolysis of a specific templated material, which is generatedin situby mixing cobalt salts, nitrogen ligands and colloidal silica, and subsequent removal of silica. Applying this novel Co-nanoparticle-based material, >100 primary, secondary, and tertiary amines includingN-methylamines and selected drug molecules were conveniently prepared starting from inexpensive and easily accessible alcohols and amines or ammonia.
Switching Selectivity in Copper-Catalyzed Transfer Hydrogenation of Nitriles to Primary Amine-Boranes and Secondary Amines under Mild Conditions
Song, Hao,Xiao, Yao,Zhang, Zhuohua,Xiong, Wanjin,Wang, Ren,Guo, Liangcheng,Zhou, Taigang
, p. 790 - 800 (2022/01/11)
A simple and efficient copper-catalyzed selective transfer hydrogenation of nitriles to primary amine-boranes and secondary amines with an oxazaborolidine-BH3 complex is reported. The selectivity control was achieved under mild conditions by switching the solvent and the copper catalysts. More than 30 primary amine-boranes and 40 secondary amines were synthesized via this strategy in high selectivity and yields of up to 95%. The strategy was applied to the synthesis of 15N labeled in 89% yield.
Nickel Complexes Bearing N,N,O-Tridentate Salicylaldiminato Ligand: Efficient Catalysts for Imines Formation via Dehydrogenative Coupling of Primary Alcohols with Amines
Han, Zhangang,Hao, Zhiqiang,Lin, Jin,Lu, Guo-Liang,Zhang, Junhua,Zhang, Xiaoying
, p. 3843 - 3853 (2021/11/18)
Treatment of salicylaldiminato ligand L1H-L2H (L1H = 2,4-di-tert-butyl-6-((quinolin-8-ylimino)methyl)phenol; L2H = 2,4-di-tert-butyl-6-(((2-(diethylamino)ethyl)imino)methyl)phenol) with Ni(OAc)2·4H2O in refluxing ethanol afforded nickel complexes [(L1)Ni(OAc)] (1) and [(L2)Ni(OAc)] (2), respectively. Reaction of L3H (L3H = (2,4-di-tert-butyl-6-(((2-(pyridin-2-yl)ethyl)imino)methyl)phenol)) with Ni(OAc)2·4H2O in the presence of excess triethylanmine gave the dual ligands coordinated nickel complex [(L2)2Ni] (3). Complexes 1-3 were well characterized by high-resolution mass spectrometry, infrared spectroscopy, elemental analysis, and X-ray diffraction analysis. All the three Ni(II) complexes exhibited efficient activity and good selectivity in the acceptorless dehydrogenative coupling of alcohols and amines to produce imines and diimines. The present protocol provides an atom-economical and sustainable route for the synthesis of various imine derivatives by employing an earth-abundant nickel salt and easily prepared salicylaldiminato ligands.
One-pot, chemoselective synthesis of secondary amines from aryl nitriles using a PdPt-Fe3O4nanoparticle catalyst
Byun, Sangmoon,Cho, Ahra,Cho, Jin Hee,Kim, B. Moon
, p. 4201 - 4209 (2020/09/23)
We have developed a new catalytic method for the one-pot, cascade synthesis of unsymmetrical secondary amines via the reductive amination of aryl nitriles with nitroalkanes using a PdPt-Fe3O4 nanoparticle (NP) catalyst. The use of a bimetallic catalyst resulted in enhanced reactivity and selectivity compared to that of either monometallic Pd-Fe3O4 or the Pt-Fe3O4 NP catalyst. Using this bimetallic catalytic system, we were successful in the synthesis of various unsymmetrical secondary amines under mild conditions. However, aryl nitriles containing an electron-donating substituent were rather resistant to the reductive amination, and when hexafluoroisopropanol (HFIP) was used as a co-solvent, the reaction selectivity and yield for unsymmetrical secondary amines increased dramatically. Using the catalyst system, one-pot, gram-scale synthesis of indole was possible from 2-nitrophenylacetonitrile. Due to the magnetic property of the Fe3O4 support, the bimetallic catalyst could easily be recycled using an external magnet at least four times.
Efficient One-Pot Reductive Aminations of Carbonyl Compounds with Aquivion-Fe as a Recyclable Catalyst and Sodium Borohydride
Airoldi, Veronica,Piccolo, Oreste,Roda, Gabriella,Appiani, Rebecca,Bavo, Francesco,Tassini, Riccardo,Paganelli, Stefano,Arnoldi, Sebastiano,Pallavicini, Marco,Bolchi, Cristiano
, p. 162 - 168 (2019/12/11)
A one-pot reductive amination of aldehydes and ketones with NaBH4 was developed with a view to providing efficient, economical and greener synthetic conditions. A recyclable iron-based Lewis catalyst, Aquivion-Fe, was used to promote imine formation in cyclopentyl methyl ether, followed by the addition of a small amount of methanol to the reaction mixture to enable C=N reduction by NaBH4. The protocol, applied to a wide number of amines and carbonyl compounds, resulted in ever complete conversion of these latter with excellent chemoselectivity towards the expected amination products in the most cases. Isolated yields, determined for a selection of the screened substrates, were found consistent with the previously obtained conversion and selectivity data. Cinacalcet, an important active pharmaceutical ingredient, was efficiently prepared by the title procedure.
Efficient photocatalytic one-pot hydrogenation and N-alkylation of nitrobenzenes/benzonitriles with alcohols over Pd/MOFs: Effect of the crystal morphology & “quasi-MOF” structure
Bian, Fengxia,Cheng, Hongmei,Jiang, Heyan,Liu, Xingyan,Long, Xingyu,Yang, Chaofen
, p. 121 - 131 (2020/06/23)
One-pot multi-step reactions over visible-light induced catalysis feature the sustainable green process. Here, ligand structure change and 2-MI coordinated modulation were adapted to adjust the crystal size, morphology and crystalline structure of Fe-MOFs; double solvent impregnation was employed for the Pd loading; “quasi-MOF” materials with retained morphology were formed with calcination under N2. Above modified materials were employed as multifunctional photocatalysts for highly efficient one-pot hydrogenation and N-alkylation of nitrobenzenes or benzonitriles with alcohols after in situ Pd photoreduction. Photocatalytic performance was evidently affected by the Fe-MOFs crystal size, morphology, crystalline structure alteration and “quasi-MOF” construction. One-pot hydrogenation and N-alkylation of benzonitriles with alcohols was achieved with excellent catalytic performance firstly in heteroegeneous catalysis. Reaction mechanism was proposed with the assistance of in situ DRIFTS.
Ultra-small cobalt nanoparticles from molecularly-defined Co-salen complexes for catalytic synthesis of amines
Beller, Matthias,Chandrashekhar, Vishwas G.,Gawande, Manoj B.,Jagadeesh, Rajenahally V.,Kalevaru, Narayana V.,Kamer, Paul C. J.,Senthamarai, Thirusangumurugan,Zbo?il, Radek
, p. 2973 - 2981 (2020/03/27)
We report the synthesis of in situ generated cobalt nanoparticles from molecularly defined complexes as efficient and selective catalysts for reductive amination reactions. In the presence of ammonia and hydrogen, cobalt-salen complexes such as cobalt(ii)-N,N′-bis(salicylidene)-1,2-phenylenediamine produce ultra-small (2-4 nm) cobalt-nanoparticles embedded in a carbon-nitrogen framework. The resulting materials constitute stable, reusable and magnetically separable catalysts, which enable the synthesis of linear and branched benzylic, heterocyclic and aliphatic primary amines from carbonyl compounds and ammonia. The isolated nanoparticles also represent excellent catalysts for the synthesis of primary, secondary as well as tertiary amines including biologically relevant N-methyl amines.
Synthesis and evaluation of Zn(II) dithiocarbamate complexes as potential antibacterial, antibiofilm, and antitumor agents
Maurya, Vinay Kumar,Singh, Ashish Kumar,Singh, Ravi Pratap,Yadav, Shivangi,Kumar, Krishna,Prakash, Pradyot,Prasad, Lal Bahadur
, p. 3338 - 3358 (2019/11/26)
Four complexes having the formula [Zn(L)2] [L1 = (C18H20NS2 –), N-(4-isopropyl-benzyl)-(benzyl)-dithiocarbamate], [L2 = (C10H12NS2 –), N-(benzyl)-(ethyl)-dithiocarbamate], [L3 = (C19H22ONS2 –), N-(4-isopropyl-benzyl)-(4-methoxy-benzyl)-dithiocarbamate], and [L4 = (C16H16NS2 –), N-(benzyl)-(4-methyl-benzyl)-dithiocarbamate] have been contemplated, synthesized, and characterized by elemental analysis and IR, 1H, 13C NMR and UV–visible absorption spectra. All Zn(II) complexes have similar geometry and coordination number. Complex A2 (with ligand L2) crystallizes in triclinic system with space group P-1 having distorted square pyramidal geometry which was stabilized by weak C–H···π and C–H···S intramolecular interactions. The antibacterial, antibiofilm, and antitumor activities of the complexes have been screened and A2 and A3 showed their prominence. Interestingly, both A2 and A3 showed more killing potential against multi-drug resistant gram-positive isolates with MIC indices of 16 μg mL?1 and 16 μg mL?1, respectively, against both MRSA and MSSA, while the antitumor agent A3 showed its prominence with GI50 and LC50 41.15 and 133.73 μg mL?1, respectively.
HYDROGENATION OF IMINES WITH RU COMPLEXES
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Page/Page column 33-34; 36-38, (2019/09/18)
The present invention relates to the field of catalytic hydrogenation and to the use of ruthenium complexes having a bidentate diphosphine ligand or two monodentate phosphine ligands, two carboxylate ligands and optionally a diamine ligand in hydrogenatio
Preparation of the Ru3(CO)8-pyridine-alcohol cluster and its use for the selective catalytic transformation of primary to secondary amines
Singh, Ajeet,Mobin, Shaikh M.,Mathur, Pradeep
, p. 14033 - 14040 (2018/11/23)
The synthesis of pyridine alcohol based ruthenium carbonyl clusters Ru3(hep)2(CO)8 (1), Ru3(hpp)2(CO)8 (2), and Ru3(bhmp-H)2(CO)8 (3) {hep-H = 2-(2-hydroxyethyl)pyridine, hpp-H = 2-(3-hydroxypropyl)pyridine and bhmp-H2 = 2,6-bis(hydroxymethyl)pyridine} has been carried out by the reaction of the corresponding pyridine-alcohol ligands with Ru3(CO)12. Clusters 1-3 have been characterized using elemental analysis, NMR, FT-IR, mass spectrometry and single-crystal X-ray structures. The clusters were explored for the selective catalytic transformation of primary amines into secondary amines using alcohols as the mono-alkylating agents via hydrogen transfer reactions. All three display efficient catalytic activity with 1 being the most effective.
